


I don't even date!

by obviouslyelementary



Category: Gotham (TV)
Genre: Blind Date, Dating, M/M, One Night Stands, One Shot Collection, Oswald Cobblepot and all his men, Romance, Technically not an AU, all the cliches, for a tumblr prompt, i dont even have official tags for this, oswald dates a lot of people, thats how i should call this fanfic
Language: English
Status: In-Progress
Published: 2019-04-04
Updated: 2019-04-07
Packaged: 2020-01-04 20:08:49
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 4,567
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18350831
Author URL: https://archiveofourown.org/users/obviouslyelementary/pseuds/obviouslyelementary
Summary: Oswald Cobblepot doesn't date, his mother would know about it.Or... would she?(A collection of one shots about the many dates Oswald Cobblepot had during all his life)((For a tumblr prompt))Edit: This is Nygmobblepot end game and for those waiting for Nygmobblepot, just read this when its complete because it will only show up in the last chapter thank you





	1. High School Crush

**Author's Note:**

> I'll make sure to tag the chapter's couple every chapter! This one is Oswald/Original Character! Enjoy!

The first date Oswald ever had was with a boy at his local high school. They didn't know each other very well, all they knew was that the other kids in school didn't like them, and that they ended up doing everything together out of pure exclusion of anyone else. They were both ugly, they were both extremely quiet, they were both weird, and they kind of fit together.

And it was Oswald's first crush, as strange as it sounded. Later he would acquired a much more refined taste, but for a first, there was no problem going to the cinema and having a few laughs and sharing a popcorn and a soda.

It was quite enjoyable when he thought back at it actually. They talked all afternoon about the dumb movie they had watched, bragged about how they could do it all much better, reacted the scenes and stayed together in the street next to Oswald's building way later than they had planned to stay.

As sweet as it was, with the moonlight shining above them and the stars twinkling above, Oswald never felt as awkward as he did when the boy leaned closer, stealing a soft kiss from his lips, the first kiss he ever gave and received.

He was 14 at the time, and he came back home with the ticket of the movie still in hand, blushing from head to toe, his heart hammering in his chest because he had never felt anything like it. It was puppy love, he would learn that after long, long years, but it was his first romantic experience, and with a boy. His dream come true.

They saw each other a few other times, went on cute dates and even shared food during school, but eventually they drifted apart, and Oswald didn’t really miss him, he didn't even remember his name, but he did miss the feeling it gave him.

The feeling of being wanted and cared for, and kissing, oh, kissing was amazing.

He wanted to do that again, and as he left school and entered the world of crime, eh decided that sure, he would give it a go.

The men in Gotham's underworld were probably way less sweet than that kid from his high school, but Oswald had nothing to lose.

And every night, as he returned home, since the day where he kissed a boy for the first time, he repeated the same phrase to his mother:

"I don't even date."

Even if he did.


	2. Butch's birthday gift

**Summary for the Chapter:**

> Pairing: Oswald Cobblepot/Butch Gilzean
> 
> Raiting: teen and up
> 
> Warnings: making out and implied sex

He got into the job with Fish when he was closing in on his twenties. He was naïve, young and filled with ambition, and he was sure that Fish Mooney would teach him everything he did and didn't know, and all he needed to know about the underworld of Gotham.

And being by her side, it would also give him free or at least easier access to all city's secrets, all mafia deals and all the dates he could ever imagine.

But first, Oswald needed to gain her trust. And slowly, year by year, she saw him less of a side character, and more like the true loyal servant he really was. She made him her umbrella boy when he was twenty two, and that was what he was known for, her umbrella boy. He went everywhere with her, to every meeting, to every single reunion, everywhere, every time, he was next to her.

And because of that, he was also always very close to her right hand man, mister Butch Gilzean.

Butch was a loyal puppy in the hands of Fish. He did all her dirty work, worshipped her as a mother and loved her as a lover, which by mafia standards was probably very usual but for Oswald, it was extremely weird. And yet, Fish put all her trust in Butch's hands, and all the secrets that Oswald did not know (the few that were indeed too personal or too close to her weak points), Butch knew.

So it was obviously that he had to win Butch's trust to get hand in hand with Fish.

And that was what he tried to do, all the time.

Apart from being extremely small compared to Gilzean, Oswald was also pretty delicate. The man was brute, only two years older than him, but huge and very smart. Usually people that big were stupid, but not Butch. No, he had the mind of a clock maker and the eyes of a hawk. He saw and heard everything, and he was suspicious of everyone, including Oswald. He kind of hated Oswald actually which made his job even harder.

To be liked by Butch Gilzean... what an honor.

So, Oswald did everything he needed to do to get to Butch's good side without being extremely obvious. It was hard the first times, and Butch always seemed to get his intentions right, which caused him a few denials and even some scarring from Fish, but in the end, nothing major seemed to be caused by his need to be better to Butch. And then he found out, during a night out with Fish, Butch and a few other mafiosos, that he was a big fan of poker night.

That was the information Oswald needed.

Behind phone calls and using Fish's name, he organized a big poker game with most of the underdogs mafiosos of the region. Only Butch's friends, no Fish, no Maroni, no Falcone, no one with big names and expectations. Just a nice poker night involving drinks, girls, money and maybe a gun or two, just in case. And, it was on Butch's birthday. All to get him settled and happy for the big reveal at the end of the party.

That that was little _Penguin's_ birthday gift for him.

Ugh how did he hate that nickname.

But if it would make Butch happy for one night at least, he would deal with it.

Everything went on smoothly. Everyone came, even Butch, and they all had a very good time. Oswald watched everything from behind the curtains, because first he wasn't good at poker, and second he just wanted Butch to be happy and drunk when he showed up. So he waited and watched as Butch won over several games, and laughed out loud with his friends as he celebrated his birthday. It was around five in the morning when the game was finally over, and everyone returned home, leaving Butch and Fish's men alone.

Right on cue, one of them said the real owner of the party was waiting for Butch in the back. And Butch stood, with a grin on his face and a calm demeanor for such a big, strong man.

He surely thought it was Fish.

What a surprise he would have.

Oswald waited by the warehouse's garage, alone, unprotected. Of course he had like two guards with guns in the shadows, in case things went south, but he didn't think they would. Besides, even if they did, killing Butch would be a horrible mistake on his part. They were only there to contain him.

Still, there was a kind of bubbling sensation in his stomach. He wasn't sure if it was the whole thought of what he had done or the possible punch bag he would become when Butch saw him there. But still, he was nervous.

"Fish!" Butch called, before he even walked out into the garage. "I can't believe you-"

He cut his speech immediately as he saw Oswald standing there, leaning on his umbrella, giving him a side smile.

"Not Fish, not tonight" he said, all kind smiles and soft demeanor. Usually he wore that suit of confidence that didn't let people close to him, but tonight it was all about partying. Butch seemed surprised, his eyes wide. "I know you expected her to be here, but I requested that I organized and gave you your birthday party this year. I hope you had fun."

"You... did all of that?" Butch asked, walking closer to him, and his expression was mixed between a happy surprise and extreme suspicion. "What for? What did you gain with it?"

"As impressive as this might sound I gained nothing actually" Oswald said, relaxed, staring up at Butch as he stopped around three feet away from him. "This was more like a present, you might say. One comrade to another."

"I don't believe you for a second. All you do is to gain something in return" Butch said, always knowing Oswald so well. But Oswald just smiled. He was confidant, and Butch was drunk.

"Yes. You are right. And tonight was so I could gain your friendship" he said, tilting his head. "You and I started with the wrong foot. Tonight was my way of fixing it. I hope it worked, Gilzean."

After a moment of silence, Butch walked to his, his face dark and serious like every time when he talked to someone that had betrayed or hurt Fish. He had only looked at Oswald like that a few times, and it still sent a shiver down his spine. Oswald walked back as Butch walked close, until the huge man grabbed him by the suit and pressed him against the nearest wall, making him groan quietly in pain. He was indeed too delicate.

"You are planning something" Butch whispered, and his breath smelled like alcohol. It was disgusting. But fine. Oswald raised his head and stared into Butch's eyes.

"I am not. I wanted to give you a present, from Fish's servant to her right-hand man" he said, firmly. He knew Butch liked when he was put in his place. So there. He was in his place. "From her umbrella boy to her favorite man."

That seemed to make Butch less violent. His hands relaxed a bit against Oswald, but did not let go. The moment was silent, as they stared at each other, both knowing very well the reason why the other was acting like that. Butch could see through Oswald's lies, he was sure, but he couldn’t act on it. Not with Fish so close to him.

And then, he smirked.

"Let's see how much you really want this, or if it is just one of your stupid games, Penguin" he said, and the rage immediately flooded Oswald's veins, but he refused to act on it. He just sighed and blinked a few times, before looking back at Butch.

"Do whatever you want to me. It is your night after all" he said, simply, letting his guard down. Fine. He would be a punchbag for the sake of Butch's trust. But the invite... seemed to be taken very differently by Butch's mind.

He stared at Oswald for a long time before his hands tightened against his suit again and he leaned in, getting Oswald into a very intense and hard and booze-tasting kiss.

That was the last thing Oswald expected to happen that night. And that was saying something.

If he was being honest, kissing Butch Gilzean was not one of the things in the top of his 'to do' lists. Sure, sometimes, when he was really drunk and he wanted to imagine someone just doing something to him, Butch would eventually show up along a list of at least 20 hot men he knew from all Gotham, manly because of his connections to Fish and his size. It intimidated Oswald in the nicest of ways, knowing full well that Butch could pick him up and do whatever he wanted with him without as much as breaking a sweat. He was so small, tiny and gentle close to Butch's brute and wide manners, it was more like a powerplay than anything. But it had never gone beyond his imagination, he didn't even try to do anything like that with Butch.

And yet, Butch's drunk mind seemed to interpret 'do whatever you want' as a sexual thing, and if it did, Oswald was surely not complaining.

It took him a second to answer the kiss, and his hands pressed back against the wall because he was sober and he had no idea if he was allowed to even touch Butch on that moment. Butch, however, seemed very interested in touching Oswald despite of their mutual distrust, deepening the kiss and pressing them together, squeezing Oswald against the wall.

Then, he pulled back to breathe, and Oswald looked up at him with his bright, shining eyes, hands finally reaching out to hold Butch's shirt, because even if this wasn't in his plans, he didn't really feel like waiting around and giving time a chance. This was better than what he had planned, and if he could get Butch on a bed with him, that would be the biggest proof that he could be trusted, and if it didn't work, it would be Oswald's biggest blackmails against Butch.

He wasn't letting that go.

So he leaned back in and kissed him again, and Butch responded immediately, sliding his hands down Oswald's body and feeling him until he reached his legs. He picked Oswald up as easy as picking up a feather and he couldn't help but moan against Butch's mouth because if the fiery spark that ran through his body at how easy he would be manhandled by the giant man.

He was enjoying it all too much, but then again, it would probably be a lifetime experience.

Luckily, Butch knew the warehouse enough to know that there was a back room connected to the garage.

They went there right away, and stayed there until noon, when Butch's mind began to finally sober up enough to realize what they had been doing for at least a few hours now.

Oswald could add an 'extreme success' in his list of plans for that one.

And when he got home late at night, he rolled his eyes at his mother's insistence of him going out with a random whore.

"Mother, I don't even date."

It was easier to explain it that way.

**Notes for the Chapter:**

> (for those that want to know im considering this Oswald's first time so like take the implications as you please)


	3. Gordon's drunk time

**Summary for the Chapter:**

> Pairing: Gobblepot (Oswald Cobblepot/James Gordon)
> 
> Warnings: implied sex; drinking

****

During his time as Fish's underdog, Oswald had many, many one night stands. He also had a few dates, and proudly enough, even a few boyfriends. Most people slept with him for pure interest in Fish's plans, but he knew how to sort out his secrets nicely. Some others he found at bars during nights out and just ended up being invited for a nice wine and a sleepover at their usually small apartments. And every now and again, someone tried to get his attention for a commitment relationship that usually did not work, mainly because Oswald was painfully aware that in the world of mafiosos, loving someone could be ones biggest mistakes.

However, as used as he was with the amount of men he had been with, slept with and even liked, nothing could prepare him for the GCPD scout boy that would show up right in time for his perfect plan of escape.

James Gordon was a sight to sore eyes, a golden retriever at heart and a little bit corrupted in the nicest of ways. And he caught Oswald's attention like a bomb in a sonar. He was painfully aware of the blond man's existence at every time of the day, and even talked about him to his mother at some point.

It was like a beautiful crush he couldn't really act on, but oh if he wanted to.

Now, he was working for Maroni, while being an underground snitch for Falcone, while Fish thought he was dead, and yet, he still needed to do Jim Gordon some favors. It was obvious that the detective wanted nothing more than Oswald out of his line of sight, but there was no way he was letting that man escape his view. He had connections, he was in the GCPD, and most important, he had saved Oswald's life and refused to kill him after he returned. He was the nicest man Oswald Cobblepot had ever known, and if that didn't warm up his heart, he didn't know what would.

Of course, there was always the problem that he had a fiancé and he was as straight as a pencil, but fine, things could be arranged and Oswald's feelings could come later. But eventually, without really doing anything, the tides turned to his side and whoever that blond girl James was with was, she decided to get out of his life, leaving him open for any type of approach.

And during his transition from the GCPD to Arkaham, James had a lot of time alone in and out of bars to think about his life.

Oswald just happened to know where he usually went to.

"Rough day Jim?" he asked as he approached the man, sitting on the stool next to him and ordering a champagne. James looked at him with a side eye and then sighed, downing his glass of whiskey and pouring some more.

"What do you want Oswald?" he asked before he took another gulp, pouring even more whiskey after that just as Oswald's fancy champagne arrived.

"To comfort an old friend" he said, sipping from his tall glass and smiling when James gave him an awfully suspicious look. "I'm being honest. I know how you feel, Jim."

"Oh so you know how to it feels to be left by your almost wife and transferred to a local asylum?" he asked, sarcastically, and Oswald crossed his bad leg over his good, putting his trusty umbrella underneath the counter.

"I know what is like to lose everything you love" he said, with a  sympathetic smile and a new sip of his drink. "You and I are not that different James. We are just the opposite sides of the same coin."

"Oh really? And how is that?" James asked, turning to face Oswald and sipping on his drink, taking it slower now. "Enlighten me, Oswald."

"You are the good side, and I am the bad" Oswald said, his voice smooth as silk, and then leaned closer, until their faces were inches apart. "But the end goal is the same. Make Gotham a better place. We love this city Jim, you and I. There is nothing we wouldn't do to protect her."

James didn't answer, he just let out a quiet huff and downed his next glass. Then, he grabbed his coat and turned to leave, but Oswald caught his wrist mid act and stood up in front of him.

"What now Oswald?"

"Let yourself relax a little, Jim" he said, voice calm, movements secure. His finger slid into James' shirt and pressed against his wrist gently, feeing his accelerated heartbeat. Those were all good signs, just like Jim's intense glance and the rapid rise and fall of his chest. "We are friends, are we not?"

"No, we are not" James answered, his voice cold, but Oswald felt not fret. He slid his fingers further into James' sleeve, sensing the shiver he felt and how tense he had become. He was quiet, and his fierce eyes stared at Oswald like he wanted to kill him.

"Then let's not be friends" Oswald agreed, leaning closer, and Jim didn't back up. He never did. "Allow me to help you relax."

He knew he could never make the first step. He needed to get James used to the idea. And luckily Gordon's drunk mind seemed less worried about reason and more worried about what he felt, because after a quick glance around the bar, he grabbed Oswald's arm and took him outside towards the alley, like a policeman took a criminal to jail. Firm and rough and sending shivers down Oswald's spine.

Then, he pushed Oswald against the dirty alley wall like he had already done so many times, but now, it was different. His eyes travelled up and down Oswald's small body and without a shadow of doubt, he moved closer, grabbing him by the suit and pulling him up before kissing him hard, all teeth and tongue. And Oswald melted into it, feeling the heat bubbling inside his belly as he tasted the whiskey in Jim's mouth and felt the press of his body against his own.

It was more he could ever ask for.

For a single moment, labels were forgotten, and they were just a horny pair making out in a dirty alley, in the darkness of the night. And Jim had no intention to stop either, grabbing Oswald by his thighs and lifting him up, grinding their bodies together in a friction that was leaving Oswald insane.

They kissed and touched and it was dirty and raw, in public and produced by the need and want coming from James' drunk mind and Oswald's lonely heart, but somehow, the pieces fit and they pressed together in a dance that was only their own.

And when it was over, Oswald expected silence and a quiet 'we will never talk about this', but instead he received a kiss that left him even more breathless that their quick time together, and a ride home, despite James' drunken state.

When he walked through his mother's door, all dirty and sweaty and wet in all the wrong places, he let out a relieved sigh knowing she was asleep. He took a quick shower, to wash off all the evidence of what had happened, and washed his clothes for the same reason, before going to bed and sleeping a peaceful amount of time.

And as he woke up, checking himself on the mirror, he noticed a big purple bruise on his neck that was surely not going to be easy to hide.

His mother insisted it was a whore's doing, but once again, he did not date.

It was just a nasty bug bite, that was all.

**Notes for the Chapter:**

> i am having so much fun with this fanfic someone stop me


	4. Drink night with Zsasz

**Summary for the Chapter:**

> Pairing: Oswald Cobblepot/Victor Zsasz
> 
> Rating: Teen and up
> 
> Warnings: mentions of sex; implied sex relationship; light angst; Oswald doesn't like what he is doing all that much;

Victor Zsasz.

How to describe him?

Most people would say he was an unfeeling sociopath that knew how to follow the rules and was extremely loyal to the Falcones. A great shooter. Maybe someone that knew exactly when to and not to cross lines. He was, by definition, one of the smartest people that ever existed, and held no want for power or money, just kills and security over his own life.

A remarkable specimen.

But to Oswald, he was someone that knew what he wanted, and knew how to ask for it.

Oswald had been working for Carmine for well over a year now. He had been his secret snitch, and now he was out in the open, which meant he needed constant protection, and therefore, Zsasz to be by his side at all times. And he didn't care about it one bit. He knew the man was loyal to Falcone and he would do anything to protect Oswald from any harm.

And yet, Oswald silently wished that Victor would be loyal to him, instead.

But beggars could not be choosers. And for now, his role was to watch and learn as events happened in front of him.

At that moment, he sat down in one of his bar's tables, drinking some champagne and ordering some new boxes to be brought over. It was noon so the bar was closed, and he sat alone, with Victor cleaning his gun a few steps away from him, leaning against a wall.

Oswald gave him a quick glance, seeing him clean the tube of his pistol thoroughly, and then returned to his list, crossing over a name and writing another down.

"Penguin, could you come here please?" Zsasz's voice resonated in the quiet room, suddenly. Confused, and yet a bit intrigued, Oswald stood up, leaving his list behind and limping towards the bald man with a curious frown.

"Yes, Zsasz?"

"I wanted to know if you would be down for a few drinks, sometime" he said, in that nonchalant way of his, pulling out a very dirty rug from inside the cane of his pistol and making a displeased face at it. Then he put it away, and looked over his shiny gun, before looking down at Oswald.

Oswald himself was... well, confused, to say the least.

"Do you want a drink? Is that what you want?" he asked, because honestly what did Zsasz want? He was impossible to read with that sarcastic non-sarcastic way of his. But Zsasz only lifted an non-existent eyebrow.

"No, I want to grab a drink somewhere with you. Tonight, preferably. I'm free" he said, and once more, Oswald was lost.

"Is that a date? Are you asking me on a date?" he asked, totally lost. Victor Zsasz wanting to drink with him somewhere? Why? Zsasz just stared at him with those unexpressive eyes of his and then chuckled.

"If you want to think as such, I don't mind. I'm more worried in the aftermath" he said, and then held the tube of his pistol against Oswald's chin, lifting his head. "Butch told me once you were a great stress reliever."

Well, first of all, Zsasz never looked stressed. He didn't look stressed now and he never did, even when he couldn't complete a job. So the implication didn’t seem to fit.

Second of all, Butch told Zsasz he was a stress reliever? Oh great. More humiliation to add to his countless list. How many times he and Butch had slept together? Five, maybe six, in whole ten years of working together? So he was the stress reliever? Wonderful.

Feeling the anger travelling through his veins, Oswald pushed the gun away and narrowed his eyes towards Zsasz, angrily.

"Don't ever call me that again" he said, firmly, and Zsasz lifted up his gun in sign of peace. Then, Oswald sighed and nodded. "Fine, a drink somewhere and then your place. Or here, whichever you prefer. Now excuse me, I have better things to do."

He turned his back to Zsasz, something no one would normally advice, and returned to his list, feeling even worst. Great, now asides from being 'Penguin' he was also 'stress reliever'. He wondered if James saw him like that too, after their little night together. He probably did, but then again, boy scout would never admit to himself that he enjoyed Oswald's presence in his bed that night. Just as he never thought Butch would but surprise surprise, he had been marketed all around the mafiosos as a good fuck toy.

It was probably because of his petite size and how uncontrollably angry he was all the time. Sure the sexual tension everyone needs. Maybe they just liked the powerplay of putting him back in his place. That was probably what it was all about.

Just as arranged he went out with Zsasz that night after the club opened, and drank enough to somewhat forget why he was so angry in the first place. Since Zsasz was nothing but a good looking man, and he had some assertive ways that lead Oswald into the most incredible sensations ever, he let him do whatever he wanted while his drunk mind and body could handle, and around five am, when they were finally over, he called a cab and went back to his mom's, wondering if she would ask about his timing again.

She did, and this time, the only thing that came to his mind was that maybe he was becoming the whore his mother was so afraid would break his heart.

And yet, even so, he did not date. Ever.

**Notes for the Chapter:**

> i'm sorry but i had to add a little bit of angst I can't live without it


End file.
